Title: Downtown Bridgeport Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $563 Expedia.ca [Downtown Bridgeport Travel Guide](https://expedia.ca/Bridgeport-Downtown-Bridgeport.dx945814454067929088)[Hotels in Downtown Bridgeport](https://expedia.ca/Downtown-Bridgeport-Hotels.d945814454067929088.Travel-Guide-Hotels)[Flights to Bridgeport](https://expedia.ca/Cheap-Flights-To-Bridgeport.d525.Travel-Guide-Flights)[Things to do in Bridgeport](https://expedia.ca/Things-To-Do-In-Bridgeport.d525.Travel-Guide-Activities)[Downtown Bridgeport Car Rentals](https://expedia.ca/Car-Rentals-In-Downtown-Bridgeport.d945814454067929088.Car-Rental-Guide) ![](https://images.trvl-media.com/place/525/4bef21ce-214e-4f25-a250-e3f317242367.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Downtown Bridgeport Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Mark Ferg - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Top Holiday Package Deals in Downtown Bridgeport Price found within the past 48 hours. Click for updated prices. ![Best Western Executive Hotel Of New Haven - West Haven](https://images.trvl-media.com/lodging/1000000/30000/23300/23217/b63e42e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Best Western Executive Hotel Of New Haven - West Haven CA $563 per person Mar 31 - Apr 4 found 1 day ago Roundtrip flight included Toronto (YYZ) to New Haven (HVN) 8/10 Very Good! (1,457 reviews) Very good, I recommend it. Reviewed on Feb 12, 2026 ![Hyatt Place Milford / New Haven](https://images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/0336d577_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Place Milford / New Haven CA $628 per person Mar 31 - Apr 4 found 1 day ago Roundtrip flight included Toronto (YYZ) to New Haven (HVN) 8.6/10 Excellent! (1,184 reviews) Overwhelming smell of deodorizer as soon as you enter the front door. A different scent in the room. 10:45 a, Housekeeping was knocking on my door. Check out is at 12p. Do not disturb sign, was on the door Reviewed on Feb 9, 2026 ![Graduate by Hilton New Haven](https://images.trvl-media.com/lodging/38000000/37210000/37200100/37200005/f203cc93_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Graduate by Hilton New Haven Downtown New Haven CA $784 per person Apr 3 - Apr 6 found 1 day ago Roundtrip flight included Halifax (YHZ) to New Haven (HVN) 9.2/10 Wonderful! (908 reviews) Loved everything about the hotel - great location, quaint and cozy rooms, clean, friendly staff and lots of character! Reviewed on Feb 12, 2026 ![Madison Beach Hotel](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Madison Beach Hotel Madison Center CA $1,251 per person Apr 3 - Apr 6 found 1 day ago Roundtrip flight included Halifax (YHZ) to New Haven (HVN) 9.4/10 Exceptional! (336 reviews) beautiful room and views Reviewed on Dec 13, 2025 ![Quality Suites Stratford](https://images.trvl-media.com/lodging/2000000/1770000/1764400/1764336/1f6d98e1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Quality Suites Stratford CA $590 per person Mar 31 - Apr 4 found 1 day ago Roundtrip flight included Toronto (YYZ) to New Haven (HVN) 8/10 Very Good! (1,005 reviews) The room was very clean and everything worked properly. The staff members, while not native English speakers, were understandable - not something one finds everywhere. The breakfast was excellent with an excellent variety of food! Reviewed on Feb 9, 2026 ## Where to stay in Downtown Bridgeport Find the best Downtown Bridgeport areas and neighborhoods for the activities you enjoy most. [Learn more about Downtown Bridgeport](https://expedia.ca/Bridgeport-Downtown-Bridgeport.dx945814454067929088) ![A beautiful Autumn 2017 sunset at Seaside Park in Bridgeport, Connecticut, USA.](https://images.trvl-media.com/place/6347879/74710af6-1b7b-4692-99d1-ffecb4fc9af6.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Black Rock Historic District Travelers enjoy Black Rock Historic District for its beaches and restaurants. Consider checking out Longfellow Park while you're in the area. [Find hotel + flight trips in Black Rock Historic District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Black%20Rock%20Historic%20District&DestID=6347879&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### South End 3 out of top 10 points of interest in this area While visiting South End, you might make a stop by sights like Seaside Park and Seaside Beach. [Find hotel + flight trips in South End](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=South%20End&DestID=983702209053167616&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Water tower at Harkness Memorial State Park](https://images.trvl-media.com/place/553248635976475205/0b803547-a46c-43f8-b2c3-f3dec3b1826a.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### West End - West Side While West End - West Side might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Seaside Beach and Seaside Park. [Find hotel + flight trips in West End - West Side](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=West%20End%20-%20West%20Side&DestID=553248635976475205&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### East End While there might not be top attractions in East End, you can explore the larger area and discover places like Total Mortgage Arena and Hartford HealthCare Amphitheater. [Find hotel + flight trips in East End](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=East%20End&DestID=553248635976482066&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Black Rock Gardens Historic District Black Rock Gardens Historic District is well-liked for its beaches and waterfront. If you're hoping to see more of the larger area, Seaside Beach and Jennings Beach are some interesting sights nearby to check out. [Find hotel + flight trips in Black Rock Gardens Historic District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Black%20Rock%20Gardens%20Historic%20District&DestID=6348195&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Downtown Bridgeport Hotel Deals ![Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min](https://images.trvl-media.com/lodging/117000000/116600000/116593700/116593683/033cca6d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min Bridgeport CT CA $166 CA $284 total Feb 16 - Feb 17 includes taxes & fees 10/10 Exceptional! (4 reviews) The host had a good response time. Apartment was easy to access, welcoming, clean, warm and cozy. It also had a bunch of goodies - from snacks to toiletries, all very much appreciated. Reviewed on Dec 17, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F02%2F2026&endDate=17%2F02%2F2026&selected=116593683&PinnedHotelID=116593683&HadPinnedHotel=true®ionId=945814454067929088) ![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### New Haven Hotel 229 George Street New Haven CT Fully refundable CA $195 CA $224 total Feb 19 - Feb 20 includes taxes & fees 9/10 Wonderful! (2,012 reviews) A+ and great location. Reviewed on Feb 11, 2026 [](https://expedia.ca/Hotel-Search?startDate=19%2F02%2F2026&endDate=20%2F02%2F2026&selected=36721&PinnedHotelID=36721&HadPinnedHotel=true®ionId=945814454067929088) ![Cambria Hotel New Haven University Area](https://images.trvl-media.com/lodging/79000000/78620000/78614500/78614483/a6a28eee_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cambria Hotel New Haven University Area 20 Dwight Street New Haven CT Fully refundable CA $160 CA $184 total Mar 8 - Mar 9 includes taxes & fees 8.6/10 Excellent! (1,011 reviews) Lovely Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=78614483&PinnedHotelID=78614483&HadPinnedHotel=true®ionId=945814454067929088) [See all 1,023 properties in Downtown Bridgeport](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=15%2F02%2F2026&endDate=16%2F02%2F2026®ionId=945814454067929088) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Discover the most popular places to visit in Downtown Bridgeport #### Hartford HealthCare Amphitheater Catch an event at Hartford HealthCare Amphitheater during your trip to Bridgeport. Stroll along the beautiful beaches or attend a sporting event in the area. [](https://expedia.ca/Hartford-HealthCare-Amphitheater-Downtown-Bridgeport.d6178252.Vacation-Attraction) #### Downtown Cabaret Theatre You can enjoy a show at Downtown Cabaret Theatre during your trip to Bridgeport. Amble around this family-friendly area's beautiful beaches or attend a sporting event. [](https://expedia.ca/Downtown-Cabaret-Theatre-Downtown-Bridgeport.d553248621532664599.Vacation-Attraction) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.